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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2623.
Published online 2009 October 3. doi:  10.1107/S160053680903894X
PMCID: PMC2971113

N′-[(E)-3-Pyridylmethyl­idene]benzo­hydrazide

Abstract

The title compound, C13H11N3O, was prepared by the reaction of benzohydrazide and nicotinaldehyde. The dihedral angle between the planes of the two aromatic rings is 47.78 (9)°. The crystal structure is stabilized by inter­molecular N—H(...)N hydrogen-bonding inter­actions.

Related literature

For related structures, see: Yin et al. (2008 [triangle]).

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Object name is e-65-o2623-scheme1.jpg

Experimental

Crystal data

  • C13H11N3O
  • M r = 225.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2623-efi1.jpg
  • a = 7.6193 (13) Å
  • b = 10.6291 (17) Å
  • c = 13.530 (2) Å
  • V = 1095.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.21 × 0.18 × 0.08 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.981, T max = 0.993
  • 5473 measured reflections
  • 1136 independent reflections
  • 612 reflections with I > 2σ(I)
  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.104
  • S = 1.18
  • 1136 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903894X/gk2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903894X/gk2228Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the National Natural Science Foundation of China (20771053), the Natural Science Foundation of Shandong Province (Y2008B48) and the Students Technology Cultural Innovation Fund of Liaocheng University (SRT08044HX2) for financial support.

supplementary crystallographic information

Comment

Acylhydrazones, as an example of Schiff bases, and their metal complexes have been widely studied due to their versatile applications in the fields of analytical and medicinal chemistry and biotechnology. These ligands, owing to their facile keto-enol tautomerization and the availability of several potential donor sites, can coordinate with metals (Yin et al., 2008). We report here the synthesis and structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. The hydrazone molecule crystallizes as an E isomer. In the crystal structure, there exist intermolecular N—H···N hydrogen bonds (Table 1). As seen in Fig. 2, the molecules are linked into one-dimensional extended chain structure.

Experimental

A mixture of benzohydrazide (10 mmol) and nicotinaldehyde (10 mmol) was refluxed in ethanol (40 ml) for 2 h at 353K. After the solution had cooled down to room temperature yellow sediment appeared. The product was crystallized from a solution of methanol to yield yellow block-shaped crystals of the title compound (yield 78%). Anal. Calcd (%) for C13H11N3O (Mr = 225.25): C,69.32; H, 4.92; N, 18.65. Found (%): C, 69.21; H, 4.97; N, 18.76.

Refinement

In the absence of significant anomalous scattering effects, Friedel pairs were averaged. The C—H and N—H H atoms were positioned with idealized geometry (N—H = 0.86 Å and C—H = 0.93 Å) and were refined using a riding model approximation with Uiso(H) = 1.2 Ueq(C, N).

Figures

Fig. 1.
The molecule of the title compound, shown with 50% probability displacement ellipsoids.
Fig. 2.
A view of the one-dimensional extended chain structure in the title compound.

Crystal data

C13H11N3OF(000) = 472
Mr = 225.25Dx = 1.365 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 764 reflections
a = 7.6193 (13) Åθ = 2.4–25.1°
b = 10.6291 (17) ŵ = 0.09 mm1
c = 13.530 (2) ÅT = 298 K
V = 1095.7 (3) Å3Block, yellow
Z = 40.21 × 0.18 × 0.08 mm

Data collection

Siemens SMART CCD diffractometer1136 independent reflections
Radiation source: fine-focus sealed tube612 reflections with I > 2σ(I)
graphiteRint = 0.073
[var phi] and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.981, Tmax = 0.993k = −12→11
5473 measured reflectionsl = −12→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.18w = 1/[σ2(Fo2) + (0.0242P)2 + 0.2399P] where P = (Fo2 + 2Fc2)/3
1136 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.20 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.1276 (5)0.7488 (3)0.4106 (3)0.0430 (12)
H10.15510.81290.37500.052*
N20.1085 (5)0.7596 (4)0.5111 (3)0.0410 (11)
N30.1881 (5)1.0185 (4)0.7966 (3)0.0450 (12)
O10.0701 (5)0.5389 (3)0.4181 (2)0.0544 (10)
C10.1015 (7)0.6334 (4)0.3688 (4)0.0386 (13)
C20.1109 (6)0.6291 (4)0.2602 (3)0.0327 (12)
C30.0535 (7)0.7257 (4)0.2001 (4)0.0438 (14)
H30.01070.79920.22850.053*
C40.0588 (7)0.7150 (5)0.0986 (4)0.0523 (15)
H40.01750.78050.05940.063*
C50.1247 (7)0.6078 (5)0.0548 (4)0.0559 (17)
H50.13010.6013−0.01370.067*
C60.1826 (7)0.5105 (4)0.1136 (4)0.0515 (15)
H60.22680.43760.08480.062*
C70.1748 (6)0.5212 (4)0.2156 (4)0.0448 (14)
H70.21320.45470.25470.054*
C80.1525 (6)0.8640 (5)0.5499 (3)0.0446 (14)
H80.19410.92880.51010.054*
C90.1968 (6)0.9926 (4)0.6998 (3)0.0432 (14)
H90.24601.05330.65880.052*
C100.1383 (6)0.8825 (4)0.6558 (4)0.0365 (13)
C110.0676 (6)0.7933 (4)0.7186 (4)0.0416 (14)
H110.02720.71730.69330.050*
C120.0567 (7)0.8168 (5)0.8183 (4)0.0492 (15)
H120.00940.75720.86100.059*
C130.1173 (6)0.9306 (5)0.8537 (4)0.0497 (15)
H130.10800.94650.92110.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.066 (3)0.036 (2)0.026 (2)−0.006 (2)0.001 (2)−0.0031 (19)
N20.051 (3)0.039 (2)0.033 (3)−0.002 (2)0.003 (2)0.0001 (19)
N30.048 (3)0.046 (2)0.041 (3)−0.003 (2)0.001 (2)−0.008 (2)
O10.080 (3)0.0399 (19)0.044 (2)−0.009 (2)−0.004 (2)0.0059 (18)
C10.043 (3)0.036 (3)0.037 (3)−0.005 (3)−0.006 (3)−0.003 (3)
C20.030 (3)0.033 (3)0.035 (3)−0.004 (3)0.002 (3)−0.004 (2)
C30.057 (4)0.033 (3)0.042 (4)0.004 (3)0.005 (3)−0.005 (3)
C40.063 (4)0.054 (3)0.040 (4)−0.002 (3)−0.007 (3)0.003 (3)
C50.077 (4)0.056 (4)0.035 (3)−0.002 (3)0.002 (3)−0.006 (3)
C60.063 (4)0.037 (3)0.055 (4)0.004 (3)0.005 (3)−0.011 (3)
C70.050 (4)0.036 (3)0.049 (4)−0.004 (3)0.000 (3)−0.001 (3)
C80.057 (4)0.039 (3)0.038 (3)−0.003 (3)0.001 (3)0.003 (3)
C90.056 (4)0.038 (3)0.036 (3)−0.002 (3)0.002 (3)0.000 (3)
C100.044 (3)0.035 (3)0.030 (3)−0.002 (3)0.000 (3)0.002 (2)
C110.045 (4)0.038 (3)0.042 (4)−0.002 (3)0.000 (3)−0.002 (3)
C120.060 (4)0.048 (3)0.039 (3)−0.010 (3)0.004 (3)0.006 (3)
C130.052 (4)0.061 (3)0.037 (3)−0.002 (3)0.004 (3)−0.006 (3)

Geometric parameters (Å, °)

N1—C11.365 (5)C5—H50.9300
N1—N21.372 (5)C6—C71.386 (6)
N1—H10.8600C6—H60.9300
N2—C81.273 (6)C7—H70.9300
N3—C131.327 (6)C8—C101.451 (6)
N3—C91.340 (5)C8—H80.9300
O1—C11.229 (5)C9—C101.386 (6)
C1—C21.473 (6)C9—H90.9300
C2—C31.380 (6)C10—C111.381 (6)
C2—C71.385 (6)C11—C121.375 (6)
C3—C41.378 (6)C11—H110.9300
C3—H30.9300C12—C131.381 (6)
C4—C51.379 (6)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.377 (6)
C1—N1—N2118.1 (4)C7—C6—H6120.0
C1—N1—H1121.0C2—C7—C6121.1 (5)
N2—N1—H1121.0C2—C7—H7119.5
C8—N2—N1117.0 (4)C6—C7—H7119.5
C13—N3—C9116.4 (4)N2—C8—C10120.4 (5)
O1—C1—N1122.5 (5)N2—C8—H8119.8
O1—C1—C2121.7 (5)C10—C8—H8119.8
N1—C1—C2115.7 (4)N3—C9—C10125.2 (4)
C3—C2—C7118.1 (4)N3—C9—H9117.4
C3—C2—C1123.4 (5)C10—C9—H9117.4
C7—C2—C1118.5 (5)C11—C10—C9116.2 (4)
C4—C3—C2121.1 (5)C11—C10—C8122.9 (5)
C4—C3—H3119.5C9—C10—C8120.9 (5)
C2—C3—H3119.5C12—C11—C10120.1 (5)
C3—C4—C5120.5 (5)C12—C11—H11119.9
C3—C4—H4119.8C10—C11—H11119.9
C5—C4—H4119.8C11—C12—C13118.6 (5)
C6—C5—C4119.2 (5)C11—C12—H12120.7
C6—C5—H5120.4C13—C12—H12120.7
C4—C5—H5120.4N3—C13—C12123.4 (5)
C5—C6—C7120.0 (5)N3—C13—H13118.3
C5—C6—H6120.0C12—C13—H13118.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.862.403.236 (5)164

Symmetry codes: (i) −x+1/2, −y+2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2228).

References

  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yin, H., Cui, J. & Qiao, Y. (2008). Polyhedron, 27, 2157–2166.

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